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WO2018179458A1 - Stratifié formant barrière aux gaz, et élément d'étanchéité - Google Patents

Stratifié formant barrière aux gaz, et élément d'étanchéité Download PDF

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Publication number
WO2018179458A1
WO2018179458A1 PCT/JP2017/020347 JP2017020347W WO2018179458A1 WO 2018179458 A1 WO2018179458 A1 WO 2018179458A1 JP 2017020347 W JP2017020347 W JP 2017020347W WO 2018179458 A1 WO2018179458 A1 WO 2018179458A1
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WO
WIPO (PCT)
Prior art keywords
gas barrier
layer
group
component
adhesive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2017/020347
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English (en)
Japanese (ja)
Inventor
健太 西嶋
健寛 大橋
達矢 泉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lintec Corp
Original Assignee
Lintec Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lintec Corp filed Critical Lintec Corp
Priority to JP2019508505A priority Critical patent/JPWO2018179458A1/ja
Priority to CN201880017227.3A priority patent/CN110392721A/zh
Priority to TW107110057A priority patent/TWI772392B/zh
Priority to KR1020197025889A priority patent/KR102496772B1/ko
Priority to JP2019509697A priority patent/JP7158377B2/ja
Priority to PCT/JP2018/011633 priority patent/WO2018180962A1/fr
Publication of WO2018179458A1 publication Critical patent/WO2018179458A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29—Laminated material
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays

Definitions

  • the present invention relates to a gas barrier laminate and a sealing body in which an object to be sealed is sealed with the gas barrier laminate.
  • organic EL elements have attracted attention as light-emitting elements that can emit light with high luminance by low-voltage direct current drive.
  • the organic EL element has a problem that light emission characteristics such as light emission luminance, light emission efficiency, and light emission uniformity are likely to deteriorate with time.
  • oxygen, moisture or the like enters the inside of the organic EL element and degrades the electrode or the organic layer.
  • several methods using a sealing material have been proposed.
  • Patent Document 1 discloses a sheet-like sealing comprising an olefin polymer having a heat of fusion and a weight average molecular weight within a specific range, and a hydrocarbon-based synthetic oil having a kinematic viscosity at 40 ° C. within a specific range. The materials are listed.
  • Examples of such a sealing material include a sealing material having a gas barrier property.
  • the sealing material is generally formed from a plurality of layers having a gas barrier layer and an adhesive layer.
  • the gas barrier layer has low affinity with the layer containing an organic compound, when an adhesive layer containing an organic compound is directly formed on the gas barrier layer, the interlayer adhesion between the gas barrier layer and the adhesive layer is reduced.
  • the gas barrier laminate thus obtained may be separated between the gas barrier layer and the adhesive layer during use. And even when placed under the high temperature and high humidity conditions as described above, separation between the gas barrier layer and the adhesive layer is difficult to occur (hereinafter, the phenomenon in which the gas barrier layer and the adhesive layer are separated).
  • the property that can be suppressed is also referred to as “adhesion between the gas barrier layer and the adhesive layer.”)
  • the gas barrier laminate having a low water vapor permeability of the adhesive layer and excellent adhesion between the gas barrier layer and the adhesive layer, and an object to be sealed are sealed with the gas barrier laminate. It aims at providing a sealing body.
  • the gas barrier layer is one or more selected from the group consisting of a gas barrier layer formed of an inorganic vapor-deposited film and a gas barrier layer formed by modifying the surface of the layer containing a polymer compound.
  • the gas-barrier laminated body of description [9] Any of [1] to [8] above, wherein a water vapor transmission rate at a thickness of 50 ⁇ m of the adhesive layer is 200 g / m 2 / day or less in an atmosphere of 40 ° C. and a relative humidity of 90%.
  • a sealed body in which an object to be sealed is sealed with the gas barrier laminate according to any one of [1] to [9].
  • the encapsulated material is at least one selected from the group consisting of an organic EL element, an organic EL display element, an inorganic EL element, an inorganic EL display element, an electronic paper element, a liquid crystal display element, and a solar cell element.
  • the gas barrier laminate having a low water vapor permeability of the adhesive layer and excellent adhesion between the gas barrier layer and the adhesive layer, and the object to be sealed are sealed with the gas barrier laminate.
  • the sealing body formed can be provided.
  • the lower limit value and the upper limit value described in a stepwise manner can be independently combined for a preferable numerical range (for example, a range of content and the like).
  • a preferable numerical range for example, a range of content and the like.
  • a preferable numerical range for example, a range of content and the like.
  • preferably 10 to 90, more preferably 30 to 60 “preferable lower limit (10)” and “more preferable upper limit (60)” are combined to obtain “10 to 60”. You can also.
  • the gas barrier laminate of the present invention comprises a gas barrier layer, an adhesion improving layer that is in direct contact with the gas barrier layer, and an adhesive layer that is in direct contact with the surface of the adhesion improving layer opposite to the gas barrier layer.
  • the adhesive layer is a layer formed from an adhesive composition containing the following components (A) and (B) (hereinafter also referred to as “adhesive composition”). is there.
  • the gas barrier laminate has a low water vapor transmission rate of the adhesive layer by satisfying the configuration, and the gas barrier layer and the adhesive layer. It will be excellent in adhesion.
  • “Gas barrier property” refers to the property of suppressing the permeation of oxygen and water vapor.
  • the thickness of the gas barrier laminate is not particularly limited, but in the embodiment in which the gas barrier laminate is used, the thickness is preferably 0.5 to 300 ⁇ m, more preferably 3 to 200 ⁇ m, and still more preferably 5 ⁇ 150 ⁇ m. When the thickness of the gas barrier laminate is within the above range, it can be suitably used when the gas barrier laminate is used as a sealing material.
  • the surface of a gas barrier layer preferably made of an inorganic vapor deposition film, a gas barrier layer containing a gas barrier resin, and a layer containing a polymer compound (hereinafter also referred to as “polymer layer”) is modified.
  • Gas barrier layer [in this case, the gas barrier layer means not only a modified region but a “polymer layer including a modified region”]. 1 or more selected from the group consisting of a gas barrier layer composed of an inorganic vapor deposition film, and a gas barrier layer obtained by modifying the surface of the layer containing a polymer compound. Is mentioned.
  • the gas barrier laminate has good adhesion between the gas barrier layer and the adhesive layer even after high temperature and high humidity conditions.
  • the gas barrier laminate of the present invention is more effective when the gas barrier layer is an inorganic vapor deposition film.
  • Examples of the inorganic vapor deposition film include inorganic compound and metal vapor deposition films.
  • Examples of the raw material for the vapor-deposited film of the inorganic compound include inorganic oxides such as silicon oxide, aluminum oxide, magnesium oxide, zinc oxide, indium oxide, tin oxide, and zinc tin oxide; inorganic nitride such as silicon nitride, aluminum nitride, and titanium nitride Inorganic carbides; inorganic sulfides; inorganic oxynitrides such as silicon oxynitride; inorganic oxide carbides; inorganic nitride carbides; inorganic oxynitride carbides.
  • Examples of the raw material for the metal deposition film include aluminum, magnesium, zinc, and tin. These raw materials for the vapor deposition film of inorganic compound or metal may be used alone or in combination of two or more.
  • the method for forming the inorganic vapor deposition film is not particularly limited, and a known method can be used.
  • Examples of the method for forming the inorganic vapor deposition film include PVD methods such as vacuum vapor deposition, sputtering, and ion plating; CVD methods such as thermal CVD, plasma CVD, and photo CVD; atomic layer deposition ( ALD method).
  • the thickness of the gas barrier layer containing the gas barrier resin is preferably 1 to 2,000 nm, more preferably 3 to 1,000 nm, still more preferably 5 to 500 nm, and still more preferably 40 to 200 nm, from the viewpoint of gas barrier properties. It is.
  • a coating method of a solution obtained by dissolving or dispersing the polymer compound in an organic solvent As a coating method of a solution obtained by dissolving or dispersing the polymer compound in an organic solvent, a bar coating method, a spin coating method, a dipping method, a roll coating method, a gravure coating method, a knife coating method, an air knife coating method, a roll knife coating method , Die coating method, screen printing method, spray coating method, gravure offset method and the like.
  • the gas barrier layer formed by modifying the surface of the polymer layer is preferably one obtained by subjecting a layer containing a silicon-containing polymer compound to an ion implantation treatment because it is more excellent in gas barrier properties.
  • silicon-containing polymer compounds include polysilazane compounds, polycarbosilane compounds, polysilane compounds, polyorganosiloxane compounds, poly (disilanylene phenylene) compounds, and poly (disilanylene ethynylene) compounds. And polysilazane compounds are more preferred.
  • the polysilazane compound is a compound having a repeating unit containing a —Si—N— bond (silazane bond) in the molecule.
  • a compound having a repeating unit represented by the following general formula (1) is preferable.
  • n represents an arbitrary natural number.
  • Rx, Ry, and Rz each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, unsubstituted or substituted
  • a non-hydrolyzable group such as an aryl group having a group or an alkylsilyl group is shown.
  • Examples of the unsubstituted or substituted cycloalkyl group include cycloalkyl groups having 3 to 10 carbon atoms such as a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the alkenyl group of the unsubstituted or substituted alkenyl group include 2 carbon atoms such as vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group. ⁇ 10 alkenyl groups.
  • alkyl group, the cycloalkyl group and the alkenyl group have a substituent
  • substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; hydroxy group; thiol group; epoxy group; glycidoxy Groups; (meth) acryloyloxy groups; unsubstituted or substituted aryl groups such as phenyl, 4-methylphenyl, 4-chlorophenyl; and the like.
  • the description of “(meth) acryloyl” means “acryloyl” and / or “methacryloyl”.
  • the description of “(meth) acryl” means “acryl” and / or “methacryl”.
  • Examples of the unsubstituted or substituted aryl group include aryl groups having 6 to 15 carbon atoms such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • alkylsilyl group examples include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-tert-butylsilyl group, a methyldiethylsilyl group, a dimethylsilyl group, a diethylsilyl group, a methylsilyl group, and an ethylsilyl group.
  • Rx, Ry, and Rz in the general formula (1) are all hydrogen atoms. Hydropolysilazane is preferred.
  • the polysilazane compound a commercially available product as a glass coating material or the like can be used as it is.
  • the polysilazane compounds may be used alone or in combination of two or more.
  • ions implanted into the polymer layer ions of rare gases such as argon, helium, neon, krypton, and xenon; ions of fluorocarbon, hydrogen, nitrogen, oxygen, carbon dioxide, chlorine, fluorine, sulfur, etc .; methane, ethane Ions of alkane gases such as ethylene and propylene; ions of alkadiene gases such as pentadiene and butadiene; ions of alkyne gases such as acetylene; aromatics such as benzene and toluene Examples include hydrocarbon gas ions; cycloalkane gas ions such as cyclopropane; cycloalkene gas ions such as cyclopentene; metal ions; organosilicon compound ions; These ions may be used alone or in combination of two or more. Among these, ions of rare gases such as argon, helium, neon, krypton, and xenon are preferable because ions can be more flu
  • the amount of ions implanted can be determined appropriately according to the purpose of use of the gas barrier laminate (necessary gas barrier properties, transparency, etc.), etc.
  • the thickness of the region into which ions are implanted by ion implantation is It can be controlled by the injection conditions such as the type, applied voltage, and processing time, and may be adjusted according to the thickness of the polymer layer and the purpose of use of the gas barrier laminate, but is preferably 10 to 400 nm.
  • the ion implantation can be confirmed by performing an elemental analysis measurement in the vicinity of 10 nm from the surface of the polysilazane layer using X-ray photoelectron spectroscopy (XPS).
  • XPS X-ray photoelectron spectroscopy
  • the gas barrier layer may be a single layer or multiple layers.
  • the layer adjacent to the adhesion improving layer is preferably a gas barrier layer made of an inorganic vapor deposition film.
  • the thickness of the adhesion improving layer is not particularly limited, but is preferably 700 nm or less, more preferably 50 to 700 nm, still more preferably 100 to 500 nm, and still more preferably 150 to 400 nm. Since the thickness of the adhesion improving layer is 700 nm or less, it is advantageous in that the gas barrier laminate can be thinned when the gas barrier laminate of the present invention is applied to an article that requires downsizing such as a portable terminal. It is. Moreover, if the thickness of the adhesion improving layer is 50 nm or more, the thickness of the adhesion improving layer becomes more uniform, and the effect of improving the adhesion between the gas barrier layer and the adhesive layer is more stable.
  • the adhesion improving layer is preferably a layer containing an organic substance. Specifically, a layer containing a polyester resin; a layer containing an acrylic resin; a layer made of a cured product of a curable composition containing an energy ray-curable compound such as a polyfunctional acrylate compound or a polyfunctional urethane acrylate compound; A layer made of a cured product of a curable composition containing a thermosetting resin such as a curable epoxy resin or a melamine resin.
  • the adhesion improving layer is preferably a layer made of a cured product of a curable composition containing a thermosetting epoxy resin.
  • adhesion between the gas barrier layer and the adhesive layer in particular, an adhesion improvement layer that is superior in the adhesion after being stored under high-temperature and high-humidity conditions. Can be formed.
  • thermosetting epoxy resins an epoxy resin containing an aromatic ring in the molecule is preferable.
  • These thermosetting epoxy resins may be used alone or in combination of two or more.
  • the curable composition may contain a silane coupling agent.
  • the adhesive improvement layer excellent in adhesiveness with a gas barrier layer can be formed.
  • silane coupling agent examples include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyltrimethoxysilane, and 3- (2-aminoethyl) aminopropyltriethoxy.
  • the content of the silane coupling agent is preferably 0.01 to 5 parts by mass, more preferably 0 with respect to 100 parts by mass of the thermosetting epoxy resin. 0.01 to 3 parts by mass.
  • the curable composition may contain a solvent.
  • the solvent include aliphatic hydrocarbon solvents such as n-hexane and n-heptane; aromatic hydrocarbon solvents such as toluene and xylene; dichloromethane, ethylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, Halogenated hydrocarbon solvents such as monochlorobenzene; alcohol solvents such as methanol, ethanol, propanol, butanol, propylene glycol monomethyl ether; ketone solvents such as acetone, methyl ethyl ketone, 2-pentanone, isophorone, cyclohexanone; ethyl acetate, acetic acid An ester solvent such as butyl; a cellosolv solvent such as ethyl cellosolv; an ether solvent such as 1,3-dioxolane; These solvents may be used alone or in combination of two or more.
  • the curable composition may contain various additives as long as the effects of the present invention are not hindered.
  • the additive include an ultraviolet absorber, an antistatic agent, a stabilizer, an antioxidant, a plasticizer, a lubricant, and a coloring pigment. What is necessary is just to adjust content of these additives suitably according to the objective.
  • the curable composition can be prepared by appropriately mixing and stirring the thermosetting epoxy resin and, if necessary, other components according to a conventional method.
  • the adhesion improving layer is applied, for example, by applying a resin composition for forming the adhesion improving layer such as the curable composition on the gas barrier layer according to a conventional method, and curing or drying the obtained coating film.
  • a resin composition for forming the adhesion improving layer such as the curable composition on the gas barrier layer according to a conventional method
  • curing or drying the obtained coating film can be formed.
  • a normal wet coating method can be used.
  • the coating film When the coating film is cured or dried, the coating film may be heated according to a conventional method.
  • the heating temperature is preferably 70 to 180 ° C, more preferably 80 to 150 ° C.
  • the heating time is preferably 30 seconds to 10 minutes, more preferably 1 to 7 minutes.
  • the adhesive layer is a layer that is in direct contact with the surface of the adhesion improving layer opposite to the gas barrier layer, and is formed from an adhesive composition containing the following components (A) and (B). Is a layer.
  • Component (B): Thermosetting resin When the gas barrier laminate has the adhesive layer, the moisture barrier property of the gas barrier laminate is further improved. Furthermore, the adhesive strength is also excellent.
  • the adhesive layer has a water vapor transmission rate at a thickness of 50 ⁇ m in an atmosphere of 40 ° C. and a relative humidity of 90%, preferably 200 g / m 2 / day or less, more preferably 150 g / m 2 / day or less, and still more preferably. Is 100 g / m 2 / day or less.
  • the lower limit of the water vapor transmission rate of the adhesive layer is not particularly limited, but is, for example, 1.0 ⁇ 10 ⁇ 6 g / m 2 / day considering the detection limit of a general-purpose measuring device.
  • the polyolefin resin refers to a polymer containing repeating units derived from olefinic monomers.
  • the polyolefin resin may be a polymer composed only of repeating units derived from olefinic monomers, or derived from monomers that are copolymerizable with olefinic monomers and repeating units derived from olefinic monomers. The polymer which consists of these repeating units may be sufficient.
  • polystyrene resin examples include very low density polyethylene (VLDPE), low density polyethylene (LDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE), linear low density polyethylene, polypropylene (PP), and ethylene-propylene.
  • VLDPE very low density polyethylene
  • LDPE low density polyethylene
  • MDPE medium density polyethylene
  • HDPE high density polyethylene
  • PP polypropylene
  • ethylene-propylene examples include copolymers, olefin elastomers (TPO), ethylene-vinyl acetate copolymers (EVA), ethylene- (meth) acrylic acid copolymers, ethylene- (meth) acrylic acid ester copolymers, and the like.
  • a carboxyl group, a group derived from a carboxylic acid anhydride, a carboxylic acid ester group, a hydroxyl group, an ammonium group, an amino group, an imide group, and an isocyanate group are preferable, and a group derived from a carboxylic acid anhydride, an alkoxy group A silyl group is more preferable, and a group derived from a carboxylic acid anhydride is particularly preferable.
  • the compound having a functional group may have two or more kinds of functional groups in the molecule.
  • unsaturated carboxylic acid to be reacted with polyolefin resin and its anhydride maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid, tetrahydrophthalic acid, aconitic acid, maleic anhydride, itaconic anhydride, glutaconic anhydride, Examples thereof include citraconic anhydride, aconitic anhydride, norbornene dicarboxylic acid anhydride, and tetrahydrophthalic acid anhydride.
  • These unsaturated carboxylic acids can be used individually by 1 type or in combination of 2 or more types.
  • maleic anhydride is preferable because an adhesive composition that is superior in adhesive strength is easily obtained.
  • Admer registered trademark
  • Unistor registered trademark
  • BondyRam manufactured by Mitsui Chemicals
  • BondyRam manufactured by Polyram
  • orevac registered trademark
  • Modic registered trademark
  • polyolefin resin that is a precursor of the silane-modified polyolefin resin
  • examples of the polyolefin resin that is a precursor of the silane-modified polyolefin resin include the polyolefin resins described above.
  • Silane-modified polyolefin resin refers to a polyolefin resin graft-modified with an unsaturated silane compound.
  • the silane-modified polyolefin resin has a structure in which an unsaturated silane compound as a side chain is graft copolymerized with a polyolefin resin as a main chain.
  • Examples include silane-modified polyethylene resins and silane-modified ethylene-vinyl acetate copolymers, and silane-modified polyethylene resins such as silane-modified low-density polyethylene, silane-modified ultra-low-density polyethylene, and silane-modified linear low-density polyethylene are preferable.
  • the modified polyolefin resin has a high content of the modified polyolefin resin in the adhesive composition, it is easy to maintain the shape of the sheet formed from the adhesive composition. From the viewpoint, those that are solid at normal temperature (25 ° C.) are preferred.
  • the modified polyolefin resins can be used singly or in combination of two or more.
  • the content of the component (A) is preferably 30 to 95% by mass, more preferably 45 to 90% by mass, and still more preferably 50%, based on the total solid content of the adhesive composition. It is -85 mass%. An adhesive composition in which the content of the modified polyolefin resin is within this range is more excellent in adhesive strength.
  • thermosetting resin Thermosetting resin
  • the said adhesive composition contains a thermosetting resin as a component (B).
  • the said adhesive composition can form the adhesive bond layer excellent in adhesive strength by containing a thermosetting resin.
  • thermosetting resin used as a component (B) a thermosetting epoxy resin, a melamine resin, a urea resin, a maleimide resin, etc. are mentioned, Preferably it is a thermosetting epoxy resin.
  • the said thermosetting epoxy resin is the polyfunctional epoxy resin demonstrated about the thermosetting epoxy resin which can be used with an adhesive improvement layer.
  • the content of the component (B) in the adhesive composition is preferably 5 to 110 parts by mass, more preferably 10 to 100 parts by mass with respect to 100 parts by mass of the component (A).
  • An adhesive layer formed from an adhesive composition in which the content of the component (B) is within this range is more excellent in water vapor barrier properties.
  • imidazole-based curing catalyst examples include 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2- Examples include phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole.
  • These curing catalysts may be used alone or in combination of two or more.
  • the content of the component (C) in the adhesive composition is preferably 0.1 to 100 parts by mass of the component (B).
  • the amount is 10 parts by mass, more preferably 0.5 to 5 parts by mass.
  • the adhesive layer formed from the adhesive composition having the component (C) content within this range has excellent adhesiveness even at high temperatures.
  • the silane coupling agent is preferably an organosilicon compound having at least one alkoxysilyl group in the molecule.
  • the silane coupling agent include polymerizable unsaturated group-containing silicon compounds such as vinyltrimethoxysilane, vinyltriethoxysilane, and methacryloxypropyltrimethoxysilane; 3-glycidoxypropyltrimethoxysilane, 2- (3, Silicon compounds having an epoxy structure such as 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 8-glycidoxyoctyltrimethoxysilane; 3-aminopropyltrimethoxysilane, N- (2 -Aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane and other amino group-containing
  • the content of the component (D) is preferably 0.01 to 5.0 parts by weight, more preferably 100 parts by weight of the component (A). 0.05 to 1.0 part by mass.
  • Examples of the method for applying the adhesive composition include various wet coating methods that can be used for forming the above-described adhesion improving layer.
  • the heating temperature during the heating is preferably 70 to 180 ° C, more preferably 80 to 150 ° C.
  • the heating time during the heating is preferably 30 seconds to 5 minutes, more preferably 1 to 4 minutes.
  • the heating temperature is preferably 40 to 90 ° C, more preferably 50 to 80 ° C.
  • the peel adhesion strength at 85 ° C. of the adhesive layer after the curing treatment is preferably 1 to 100 N / 25 mm, more preferably 5 to 50 N / 25 mm.
  • the peel adhesive strength at 85 ° C. of the adhesive layer after the curing treatment is measured by the method described in Examples described later.
  • the gas barrier laminate having the base material layer is used in the production of a sealing body or the like described later. Excellent handleability. Moreover, it becomes easy for a gas barrier laminated body to acquire self-supporting property by having a base material layer.
  • the thickness of the base material layer is preferably 0.4 to 400 ⁇ m, more preferably 0.5 to 95 ⁇ m, still more preferably 0.9 to 90 ⁇ m.
  • polymers and aromatic polymers include polymers and aromatic polymers.
  • polyester, polyamide or cycloolefin polymer is preferable, and polyester or cycloolefin polymer is more preferable.
  • polyester examples include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyarylate, and the like, and polyethylene terephthalate is preferable.
  • polyamide examples include wholly aromatic polyamide, nylon 6, nylon 66, nylon copolymer, and the like.
  • cycloolefin polymer examples include a norbornene polymer, a monocyclic olefin polymer, a cyclic conjugated diene polymer, a vinyl alicyclic hydrocarbon polymer, and hydrides thereof.
  • Apel an ethylene-cycloolefin copolymer manufactured by Mitsui Chemicals
  • Arton a norbornene polymer manufactured by JSR
  • Zeonoa a norbornene polymer manufactured by Nippon Zeon
  • the base material layer As the base material layer, a resin film produced by a known method such as a casting method or a melt extrusion method can be used. Depending on the material forming the gas barrier layer, the adhesion between the base material layer and the gas barrier layer may be poor. In this case, even if the adhesion between the gas barrier layer and the adhesion improving layer is good, peeling between the substrate layer and the gas barrier layer may occur. It is preferable that the gas barrier layer is laminated on the primer layer.
  • the primer layer may be a single layer, or may be a laminate of two or more of the same or different layers. Examples of the primer layer include a layer obtained by curing a composition containing an ultraviolet curable compound.
  • the composition containing the ultraviolet curable compound may contain an inorganic filler. Examples of the inorganic filler include silica particles.
  • the thickness of the primer layer is preferably 0.1 to 10 ⁇ m, more preferably 0.5 to 5 ⁇ m.
  • a gas barrier laminate having a base material layer can be efficiently produced by forming a gas barrier layer laminated directly or via another layer on the base material layer.
  • a method of forming a gas barrier layer using the above method after forming a direct or other layer on the base material layer can be used.
  • other layers include a primer layer.
  • a film having a layer structure laminated in the order of the base material layer / gas barrier layer or a layer structure laminated in the order of base material layer / other layer (preferably primer layer) / gas barrier layer is also referred to as “gas barrier film”. .
  • a gas barrier laminate having a base material layer can be produced through a step of providing the adhesive layer on a gas barrier film having the adhesion improving layer.
  • the gas barrier laminate may have a release film.
  • a conventionally known release film can be used as the release film, and is used for protecting the gas barrier layer, the adhesive layer, the base layer, and the like. More specifically, the release film functions as a support in the production process of the gas barrier laminate, and the protective sheet of the layer that is in contact with the release film until the gas barrier laminate is used. Function as. Further, when the gas barrier laminate has a configuration not having a base material layer, the gas barrier laminate preferably has a release film as in the layer configuration (ii) described above. When producing a gas barrier laminate having no base material layer, it becomes easy to produce a gas barrier laminate having no base material layer by using a release film that can function as a support.
  • the gas barrier laminate without the base layer is, for example, a layer laminated in the order of “base layer / gas barrier layer” in the gas barrier film in the example of the method for producing a gas barrier laminate having the base.
  • “Structure or Layer Structure Laminated in Order of Base Layer / Other Layer (Preferably Primer Layer) / Gas Barrier Layer” “Layer Structure Laminated in Order of Release Film / Gas Barrier Layer or Release Film / Other Layer” It can be manufactured by using a gas barrier film having a (preferably an underlayer to be described later) / a layer structure laminated in the order of a gas barrier layer.
  • a peeling film is peeled and removed normally.
  • peeling film substrate examples include paper substrates such as glassine paper, coated paper, and high-quality paper; laminated paper obtained by laminating a thermoplastic resin such as polyethylene on these paper substrates; polyethylene terephthalate resin, polybutylene terephthalate resin, Examples thereof include plastic films such as polyethylene naphthalate resin, polypropylene resin, and polyethylene resin.
  • release agent examples include silicone elastomers, olefin resins, isoprene resins, rubber elastomers such as butadiene resins, long chain alkyl resins, alkyd resins, fluorine resins, and the like.
  • the two release films may be the same or different.
  • the release forces of the two release films are different, problems are less likely to occur when the gas barrier laminate is used. That is, by making the peeling forces of the two release films different, the process of first peeling the release film from the gas barrier laminate can be performed more efficiently.
  • the thickness of the release film is preferably 10 to 300 ⁇ m, more preferably 20 to 125 ⁇ m, still more preferably 30 to 100 ⁇ m.
  • the gas barrier laminate has a release film and a gas barrier in order to protect the gas barrier layer. It is preferable to have an underlayer between the layers.
  • the foundation layer is provided directly on the release film.
  • the underlayer preferably comprises a cured product of a curable composition containing an energy curable resin and an inorganic filler.
  • the energy curable resin refers to a resin that is converted into a cured product when a curing reaction is started by irradiating or heating energy beams such as an electron beam and ultraviolet rays.
  • the energy curable resin is usually a mixture containing a polymerizable compound as a main component.
  • the polymerizable compound is a compound having an energy polymerizable functional group. Examples of the energy polymerizable functional group include ethylenically unsaturated groups such as a (meth) acryloyl group, a vinyl group, an allyl group, and a styryl group.
  • the energy curable resin may contain an oligomer.
  • the oligomer include polyester acrylate oligomers, epoxy acrylate oligomers, urethane acrylate oligomers, polyol acrylate oligomers, and the like.
  • the energy curable resin may contain a polymerization initiator such as a photopolymerization initiator or a thermal polymerization initiator.
  • the energy curable resin is preferably a resin curable by ultraviolet irradiation (ultraviolet curable resin).
  • ultraviolet curable resin By using an ultraviolet curable resin, a layer made of a cured product of the energy curable resin can be efficiently formed.
  • inorganic substances constituting the inorganic filler include metal oxides such as silica, aluminum oxide, zirconia, titania, zinc oxide, germanium oxide, indium oxide, tin oxide, indium tin oxide (ITO), antimony oxide, and cerium oxide; Metal fluorides such as magnesium fluoride and sodium fluoride; and the like.
  • the inorganic filler may have a surface modified with an organic compound.
  • the average particle size of the inorganic filler is not particularly limited, but is preferably 5 to 100 nm. If the average particle size of the inorganic filler is too small, it may be difficult to sufficiently improve the peelability of the release film. On the other hand, if the average particle size of the inorganic filler is too large, the gas barrier property of the gas barrier layer formed on the underlayer may be lowered.
  • the average particle size of the inorganic filler can be measured by a dynamic light scattering method using a particle size distribution measuring device.
  • the content of the resin component (component derived from the energy curable resin) contained in the underlayer is not particularly limited, but is preferably 30 to 90% by mass, more preferably 50%, based on the total amount of the components contained in the underlayer. -70% by mass.
  • the content of the inorganic filler contained in the underlayer is not particularly limited, but is preferably 10 to 70% by mass, more preferably 50 to 70% by mass, based on the total amount of components contained in the underlayer.
  • the thickness of the underlayer is not particularly limited, but is preferably 0.1 to 10 ⁇ m, more preferably 0.5 to 5 ⁇ m. If the underlayer is too thin, the gas barrier layer or the like may be destroyed when the release film is peeled off. On the other hand, if the underlayer is too thick, the bending resistance may be reduced.
  • the maximum cross-sectional height (Rt) of the roughness curve of the surface of the underlayer opposite to the side in contact with the release film is not particularly limited, but is preferably 1 to 200 nm, more preferably 2 to 150 nm.
  • the surface of the underlayer opposite to the side in contact with the release film is the surface where the underlayer is exposed when the underlayer is formed on the release film.
  • the gas barrier layer is in contact with the surface directly or through another layer.
  • the maximum cross-sectional height (Rt) of the roughness curve can be measured by observing the exposed surface of the underlayer with an optical interference microscope if the gas barrier laminate is in the process of being produced. .
  • the maximum cross-sectional height (Rt) of the roughness curve is too small, it may be difficult to sufficiently improve the peelability of the release film. On the other hand, if the maximum cross-sectional height (Rt) of the roughness curve is too large, the gas barrier properties of the gas barrier layer formed on the underlayer may be reduced.
  • the maximum cross-sectional height (Rt) of the roughness curve can be optimized by adjusting the average particle size and amount of the inorganic filler used.
  • the sealing body of the present invention is such that an object to be sealed is sealed with the gas barrier laminate. Since the sealing body is a sealing body that is sealed with the gas barrier laminate of the present invention, defects caused by delamination and / or intrusion of water vapor or the like due to delamination are unlikely to occur. . Therefore, the said sealing body can be used suitably for the use as which the performance maintenance of a to-be-sealed object is requested
  • the sealing body includes, for example, a transparent substrate, an element (an object to be sealed) formed on the transparent substrate, and a sealing material for sealing the element, What has a sealing material is the said gas-barrier laminated body is mentioned.
  • the transparent substrate is not particularly limited, and various substrate materials can be used. In particular, it is preferable to use a substrate material having a high visible light transmittance. In addition, a material having a high blocking performance for blocking moisture and gas to enter from the outside of the element and having excellent solvent resistance and weather resistance is preferable.
  • transparent inorganic materials such as quartz and glass; polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polystyrene, polyethylene, polypropylene, polyphenylene sulfide, polyvinylidene fluoride, acetyl cellulose, brominated phenoxy, aramids, polyimide , Transparent plastics such as polystyrenes, polyarylates, polysulfones, and polyolefins.
  • the thickness of the transparent substrate is not particularly limited, and can be appropriately selected in consideration of the light transmittance and the performance of blocking the inside and outside of the element.
  • the object to be sealed is selected from the group consisting of an organic electroluminescence (organic EL) element, an organic EL display element, an inorganic EL element, an inorganic EL display element, an electronic paper element, a liquid crystal display element, and a solar cell element. More than species.
  • the manufacturing method of the said sealing body is not specifically limited.
  • the adhesive layer of the gas barrier laminate is stacked on the object to be sealed, the adhesive layer and the object to be sealed are bonded by heating. Subsequently, the said sealing body can be manufactured by hardening the said adhesive bond layer.
  • the bonding conditions for bonding the adhesive layer of the gas barrier laminate and the material to be sealed are not particularly limited.
  • the bonding temperature is preferably 23 to 100 ° C., more preferably 40 to 80 ° C. This adhesion treatment may be performed while applying pressure.
  • the curing conditions for curing the adhesive layer the aforementioned conditions can be used.
  • the sealing body can be suitably used for various electronic device applications.
  • the electronic device include a liquid crystal display, an organic EL light emitter, an inorganic EL light emitter, electronic paper, and a solar cell.
  • an organic EL light-emitting body and an inorganic EL light-emitting body are provided for uses such as a display and illumination.
  • the adhesive layer of the gas barrier laminate is bonded so as to cover a cathode layer of a light emitting element in which a substrate, an anode layer, a light emitting layer, and a cathode layer are sequentially laminated.
  • An EL display is exemplified.
  • An electronic device provided with the gas barrier laminate is less prone to problems due to defects in the sealing material due to delamination or the like, or intrusion of water vapor or the like.
  • the weight average molecular weight (Mw) of the modified polyolefin resin as component (A) was measured under the following conditions using a gel permeation chromatograph (GPC) apparatus (product name “HLC-8020” manufactured by Tosoh Corporation). The value measured and measured by standard polystyrene conversion was used. (Measurement condition) Column: “TSK guard column HXL-L”, “TSK gel G2500HXL”, “TSK gel G2000HXL”, and “TSK gel G1000HXL” (both manufactured by Tosoh Corporation) Column temperature: 40 ° C. ⁇ Developing solvent: Tetrahydrofuran ⁇ Flow rate: 1.0 mL / min
  • composition for adhesion improving layer ⁇ Preparation of composition for adhesion improving layer> Thermosetting epoxy resin (Mitsubishi Gas Chemical Co., Ltd., “Maxive M-100”, 100% solid content), 100 parts of polyfunctional amine compound (Mitsubishi Gas Chemical Co., Ltd., multifunctional amine resin “Maxive C-93T”, Solid content 65.2%) 320 parts, methanol 5166 parts and ethyl acetate 586 parts were mixed to obtain a curable composition (1). The number of parts is the total amount of solid content and solvent.
  • the adhesive composition was applied onto the release-treated surface of the release film (1) (trade name: SP-PET382150, manufactured by Lintec Corporation) with a knife coater, and the obtained coating film was dried at 100 ° C. for 2 minutes. An adhesive layer having a thickness of 25 ⁇ m was formed. On the surface of the adhesive layer opposite to the release film (1), the release treatment surface of the release film (2) (trade name: SP-PET381031 manufactured by Lintec Corporation) was further bonded. In addition, using the same method, an adhesive layer having a thickness of 50 ⁇ m was obtained as a sample for measuring water vapor transmission rate separately from the adhesive layer having a thickness of 25 ⁇ m.
  • a silicon oxide film was provided as a gas barrier layer with a thickness of 100 nm by a CVD method on a primer layer having a thickness of 1 ⁇ m of a polyethylene terephthalate film with a primer layer (thickness 51 ⁇ m) to obtain a gas barrier film.
  • the adhesion improving layer composition was applied to the gas barrier layer-forming surface of the obtained gas barrier film using a Mayer bar.
  • the obtained coating film was heated at 100 ° C. for 2 minutes to form an adhesion improving layer having a thickness of 300 nm.
  • the release film (2) is peeled off from the adhesive layer having a thickness of 25 ⁇ m, and the exposed adhesive layer surface and the adhesion improving layer surface of the gas barrier film provided with the adhesion improving layer are used with a heat laminator. Bonding was performed at 60 ° C., and a gas barrier laminate was obtained with the release film (1) left.
  • Example 1 A gas barrier laminate and a sample for measuring water vapor transmission rate were obtained in the same manner as in Example 1 except that the adhesive layer was directly bonded to the gas barrier layer without providing the adhesion improving layer.
  • the adhesive layer was directly bonded to the gas barrier layer without providing the adhesion improving layer.
  • the peeling adhesion strength was not measured.
  • Example 1 except that the component (A) was changed to the acrylic copolymer and the solid content concentration of the adhesive composition was 35%, the gas barrier laminate and A sample for measuring water vapor transmission rate was obtained.
  • the peeling adhesive strength was not measured.
  • the release films (1) and (2) were removed from the water vapor transmission rate measurement samples prepared in the examples and the comparative examples, and a water vapor transmission rate measurement device (trade name: L80-5000, manufactured by LYSSY) was used. The water vapor transmission rate was measured in an environment of a temperature of 40 ° C. and a relative humidity of 90%.
  • the gas barrier laminate of Example 1 was excellent in adhesion between the gas barrier layer and the adhesive layer without the adhesive layer being transferred onto the glass plate. Furthermore, it was confirmed that the water vapor transmission rate of the adhesive layer of the gas barrier laminate of Example 1 is superior to the water vapor transmission rate of the adhesive layer of the gas barrier laminate of Comparative Example 2. Moreover, it was confirmed that the gas-barrier laminated body of Example 1 is excellent also in adhesive strength.
  • the adhesion between the gas barrier layer and the adhesive layer was inferior because there was no adhesion improving layer between the gas barrier layer and the adhesive layer.
  • the gas-barrier laminated body of the comparative example 2 is not a layer formed from the adhesive composition containing the components (A) and (B), it was confirmed that the water vapor permeability of the obtained adhesive layer was inferior. It was.
  • the gas barrier laminate of the present invention has a low water vapor permeability of the adhesive layer and is excellent in adhesion between the gas barrier layer and the adhesive layer. For this reason, the gas barrier laminate of the present invention is required to prevent the occurrence of defects due to, for example, defects in the gas barrier laminate itself due to delamination and / or intrusion of water vapor or the like, such as sealing materials for various electronic device elements. It can be suitably used in the application.
  • the sealing body of the present invention in which the object to be sealed is sealed with the gas barrier laminate of the present invention also has a problem that the sealing material itself is defective due to delamination and / or intrusion of water vapor or the like. It will be difficult. Therefore, the sealed body of the present invention can be suitably used in applications where it is required to maintain the performance of the object to be sealed over a long period of time such as various electronic device applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Laminated Bodies (AREA)
  • Electroluminescent Light Sources (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)

Abstract

La présente invention concerne : un stratifié formant barrière aux gaz ayant une couche formant barrière aux gaz, une couche améliorant l'adhérence en contact direct avec la couche formant barrière aux gaz, et une couche adhésive en contact direct avec la couche améliorant l'adhérence sur la surface opposée à la couche formant barrière aux gaz, la couche adhésive étant une couche formée à partir d'une composition adhésive contenant un composant (A) : une résine de polyoléfine modifiée et un composant (B) : une résine thermodurcissable ; et un élément d'étanchéité comprenant un article à sceller qui est scellé par le stratifié formant barrière aux gaz.
PCT/JP2017/020347 2017-03-30 2017-05-31 Stratifié formant barrière aux gaz, et élément d'étanchéité Ceased WO2018179458A1 (fr)

Priority Applications (6)

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JP2019508505A JPWO2018179458A1 (ja) 2017-03-30 2017-05-31 ガスバリア性積層体、及び封止体
CN201880017227.3A CN110392721A (zh) 2017-03-30 2018-03-23 阻气性膜以及密封体
TW107110057A TWI772392B (zh) 2017-03-30 2018-03-23 阻氣性薄膜及密封體
KR1020197025889A KR102496772B1 (ko) 2017-03-30 2018-03-23 가스 배리어성 필름, 및 봉지체
JP2019509697A JP7158377B2 (ja) 2017-03-30 2018-03-23 ガスバリア性フィルム、及び封止体
PCT/JP2018/011633 WO2018180962A1 (fr) 2017-03-30 2018-03-23 Film formant une barrière aux gaz et objet scellé de manière étanche

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CN114845873A (zh) * 2019-12-26 2022-08-02 琳得科株式会社 光学用层叠体

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TWI772392B (zh) 2022-08-01
KR102496772B1 (ko) 2023-02-06
CN110392721A (zh) 2019-10-29
WO2018180962A1 (fr) 2018-10-04
JP7158377B2 (ja) 2022-10-21
KR20190130565A (ko) 2019-11-22
TW201840415A (zh) 2018-11-16
JPWO2018179458A1 (ja) 2020-02-06

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